Vacation rentals with a pool in Madison
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madison
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Madison rentals with a pool
House rentals with a pool
Home in Galena
4.92 out of 5 average rating, 185 reviewsGalena Getaway
May 7 – 14
Home in Galena
4.97 out of 5 average rating, 125 reviewsGalena Territory Sun-Drenched TreeHouse w/ Views
Jun. 11 – 18
Home in Galena
4.97 out of 5 average rating, 125 reviewsHot tub/Game Room/Fire Pit/Across street from Pool
Feb. 2 – 9
Home in Galena
4.92 out of 5 average rating, 108 reviewsBoulder Creek
Oct. 19 – 26
Home in Lake Geneva
4.91 out of 5 average rating, 126 reviewsHome away from Home
Mar. 9 – 16
Home in Spring Green
5.0 out of 5 average rating, 22 reviewsThe Hemlock/$0 Cleaning Fee/Hot Tub/Golf
Apr. 20 – 27
Home in Delafield
4.96 out of 5 average rating, 23 reviewsCute and cozy 2 bedroom house perfectly located!
Feb. 21 – 28
Home in Middleton
4.88 out of 5 average rating, 26 reviewsSunny contemporary home with pool close to all
Nov. 15 – 22
Condo rentals with a pool
Condo in Lake Geneva
4.82 out of 5 average rating, 22 reviewsStay Awhile- Historic Hayloft Lodge
Oct. 10 – 17
Condo in Lake Geneva
4.98 out of 5 average rating, 82 reviewsMagnificient views in a Lakefront condo, Fireplace
Oct. 15 – 22
Condo in Lake Geneva
4.83 out of 5 average rating, 12 reviewsCondo in Geneva with lake views!
Dec. 18 – 25
Condo in Lake Geneva
4.88 out of 5 average rating, 49 reviewsLakeshore Dr. Condo W/ Boat Parking in Lake Geneva
Mar. 14 – 21
Condo in Lake Geneva
4.95 out of 5 average rating, 44 reviewsCozy Lake Geneva Retreat with Year-Round Views!
Jan. 6 – 13
Condo in Lake Geneva
4.98 out of 5 average rating, 45 reviewsUpdated 2BR Lake Geneva Condo
Nov. 16 – 23
Condo in Geneva
4.92 out of 5 average rating, 25 reviewsQuaint, quiet condo minutes from Lake Geneva
Dec. 2 – 9
Condo in Lake Geneva
4.94 out of 5 average rating, 31 reviewsLuxury Retreat | 2BD | Pool | Nr Lake Geneva
Jan. 15 – 22
Quick stats about vacation rentals with a pool in Madison
Total rentals
40 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
580 reviews
Nightly prices starting at
$14 CAD before taxes and fees
Destinations to explore
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Wisconsin Dells Vacation rentals
- Schaumburg Vacation rentals
- Oshkosh Vacation rentals
- Galena Vacation rentals
- Lake Wisconsin Vacation rentals
- Appleton Vacation rentals
- Sheboygan Vacation rentals
- Dubuque Vacation rentals
- Rockford Vacation rentals
- Chicago Vacation rentals
- Rentals with pools United States
- Monthly Rentals Madison
- Family-friendly rentals Madison
- Rentals with outdoor seating Madison
- Rentals with a fireplace Madison
- Apartment rentals Madison
- Private suite rentals Madison
- Waterfront rentals Madison
- Rentals with a patio Madison
- Rentals with a firepit Madison
- Pet-friendly rentals Madison
- Rentals with a hot tub Madison
- Cottage rentals Madison
- Rentals with lake access Madison
- Rentals with breakfast Madison
- Cabin rentals Madison
- Rentals with a washer and dryer Madison
- Rentals with beach access Madison
- House rentals Madison
- Kid-friendly rentals Madison
- Rentals with pools Milwaukee
- Rentals with pools Lake Geneva
- Rentals with pools Wisconsin Dells
- Rentals with pools Wisconsin
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom